This seems a little ambiguous to me. You're saying that recoup on duress (after jailer), you can still play duress, but what if you discard a deep analysis after a jailer hits play?
It comes down to timestamps. If the card has flashback itself, Jailer will remove that ability. If some other effect starts after the Jailer is already in play giving a card flashback (like recoup), then that flashback will not be removed. If after Recoup gives something flashback a Jailer comes into play, then that flashback given by the Recoup will be removed.